Cuba: Entering the last quarter of the game: 3 Questions.

[El Presidente]

As Trump and Rubio's eyes now turn from Iran to Cuba, the standoff now enters it's final phase. 

The economic siege of Cuba by the US has been effective. 

Maintenance of the status quo for either side does not appear to be an option. 

 

3 Questions. 

1. How does this end. What does that process look like? 

2. How long before this ends?

3. What is the likely end position? When all said and done, describe the post conflict/negotiation Cuba. 

[chris12381]

For context: I've been running an ongoing US-Cuba analysis with Claude (Anthropic's AI) for a few months now. Not casual chat. I built a dedicated project tracking GAESA, the Rubio pressure campaign, the Brothers to the Rescue case and the Raul Castro indictment, the Helms-Burton litigation, and the energy crisis, and I've been feeding it primary sources and making it show its work. So when you posted these three questions, I ran them through that setup. What follows is its answer, lightly edited. I made it flag which claims rest on a single anonymous scoop versus what's actually confirmed, and I told it to discount Trump's "soon" rhetoric since that's been wrong for 30 years. Take it for what it is: a structured guess, not gospel.

"Quick pushback before I answer: I don't think this is the "final phase." Calling it that is the same trap that's burned every Cuba-watcher since 1991. The siege is real and it's biting harder than anything since the Special Period, but "effective" and "about to end" are different claims.  Here's how I'd actually answer your three.

1.  How does it end / what's the process?

Most likely it doesn't end clean, at least not soon. The realistic path is a grind: more sanctions, more back-channel talks that go nowhere, the occasional concession from Havana (they've already dumped 2,000+ prisoners) that doesn't satisfy Rubio, because Rubio's actual demand is the regime itself, which is Havana's one red line. Two sides whose bottom lines can't both be true equals stalemate, not a deal. If it does resolve, watch GAESA, not Díaz-Canel. The real talks are reportedly already running through the military conglomerate and Raúl's grandson, not the formal government. An elite cutting itself a soft landing (think USSR 1991, not a clean democratic handoff) is the most plausible off-ramp. The other live path is the ugly one: a Maduro-style snatch using the Castro indictment as the legal hook. Possible, but Cuba's a harder target than Venezuela was. No single guy to grab, a much tighter security state, and Díaz-Canel promising a bloodbath for any invader.

2.  How long?

Don't hold your breath for 2026. The Iran deal just freed up the bandwidth everyone said was the holdup, and Trump's first move was to point it at Ukraine and Lebanon, not Cuba. Revealed priorities beat tweets. Add the midterm math: Florida wants action, but a Mariel-scale boatlift right before November is the last thing the border crowd wants. I'd put a regime-ending event this calendar year at maybe one-in-four to one-in-three, and basically nil in the next month barring something I can't see. Trump's "soon" is worth nothing on timing. He claimed an Iran deal was imminent something like 38 times before one actually landed.

3.  Post-conflict Cuba

Base case, and I don't love it: the regime survives in worse shape. More militarized, more repressive, GAESA running even more of the economy, leaning harder on Russia and China to keep the lights on.  Sanctions that wreck the civilian economy tend to entrench the guys holding the hard currency and the guns, which is exactly GAESA. The rosier version is a managed opening: elite-brokered transition, partial market reforms, heavy US/Treasury leverage over the books, Vietnam-ish. The version nobody should want is Iraq 2003: break the state apparatus, get chaos, an exodus across the Straits, maybe an insurgency. The thing the siege-is-working crowd keeps missing is that deprivation alone has never cracked this regime. Yet, this crisis is different, and not in Havana's favor: the oil blockade and the scale of the exodus are new, and the leadership is weaker than Fidel's was. But the mechanism that actually ends regimes is the same one it's always been. Hardship topples governments by splitting the army and the elite, not by starving the street, and that split is the thing I haven't seen yet. What would change my read is mass protest significantly bigger than July 2021, or a visible crack in the security forces. Until I see one of those, I'm betting on grind, not collapse."

[anacostiakat]

Yeah. With the Iran MOU just signed and looking at it, I don't have much confidence.  

[Dadof3]

Starving the population is not going to bring about meaningful change in the government is my guess. If the US is just going to continue the blockade and various sanctions, Trump will almost certainly get bored and turn his attention to something else at some point and nothing will really change. I think the bribery method would work best.  

[Khimerah]

It’s very hard to tell, but I do think we’ll see a focus on Cuba now. 

1. At this point it’s still too early to tell but based on Venezuela, a military operation isn’t off the table. They could be looking for someone to replace Canal as president, military officials who would be willing to support change, and likely how to do this quickly to avoid resistance. We are already seeing the Cubans fast track approve reforms to appease the U.S. but it’s very unlikely this will be enough to turn the heat off. I think personally, we’re gonna see either one of two ways it ends. Either we see an actual true free Cuba with proper elections, the embargo lifted, and the end of the PCC. The second and more likely scenario is some level of reform, certain sanctions coming off, but a skeleton of the current regime staying in place with some friendly faces to the U.S.. That second option is closer to what We see in Venezuela and most likely, but ideally the first option would be best for the Cuban people. 

2. I think we’ll see this before midterms easily, I don’t think Trump will get away with it afterwards. He’s going to need a victory after the Iran war, if Hegseth and Ratcliffe are fired then Rubio will be an even louder voice likely unopposed pushing for something to happen. 

3. Without repeating too much of my first point, in my first option you could see true fair elections taking place In Cuba, an actual free society. You’d likely see some level of compensation to those who lost property in the revolution and definitely an end of the Cuban cigar industry as we know it. In the more likely scenario I think the PCC skeleton remains, companies are allowed to participate and Cuba loosens its iron grip, but you’ll likely see some state monopoly continue to exist just restructured. I’ve seen people speculate Sandro Castro could be the president under this situation and it wouldn’t be too shocking in all honesty with how crazy this all is. I think state monopolies will exist, so Habanos exists but companies like Altadis have larger roles, more say, and more rights. It likely doesn’t allow for compensation to those who lost property, so no major lawsuits are going to happen. Americans will probably be given some ability to travel for tourism, probably get to bring Cuban products back, but the embargo will likely stay. The first option would be best for the Cuban people, they would be free and hopefully a better country rises from this. In the second option I think the Cuban people will see benefits but not to the satisfaction of all. 
 

This is just my opinion, not an expert but I have been following the topic closely. 

[Khimerah]

6 hours ago, Dadof3 said:

Starving the population is not going to bring about meaningful change in the government is my guess. If the US is just going to continue the blockade and various sanctions, Trump will almost certainly get bored and turn his attention to something else at some point and nothing will really change. I think the bribery method would work best.  

I agree with you first statement, but Rubio is likely not going to calm down on this. Regardless if Hegseth and Ratcliffe staying or leaving Trump needs a win like Venezuela, Cuba is that next win. The Cubans are feeling the heat and there’s no reason to take their foot off the gas now. 

[Dadof3]

2 minutes ago, Khimerah said:

I agree with you first statement, but Rubio is likely not going to calm down on this. Regardless if Hegseth and Ratcliffe staying or leaving Trump needs a win like Venezuela, Cuba is that next win. The Cubans are feeling the heat and there’s no reason to take their foot off the gas now. 

I agree in the short term it is going to be the focus of the Trump administration's foreign policy effort but we know the US is unwilling to risk its soldiers in actual combat right now. So I'm not sure what more the US can do right now if they do not want to use the military?  

[Khimerah]

2 hours ago, Dadof3 said:

I agree in the short term it is going to be the focus of the Trump administration's foreign policy effort but we know the US is unwilling to risk its soldiers in actual combat right now. So I'm not sure what more the US can do right now if they do not want to use the military?  

I think the pressure economically is definitely going to increase, I think if they wait it out and continue to make things more difficult there will likely a deal. I think a small Venezuela military operation definitely on the table still though. 

[BrightonCorgi]

1.  Invasion and arming of awaiting militia along with a full spectrum assault. There must be several playbooks the US has available to choose from. Cuban leadership will rollover easier than Iran. Interim government will put on trial many of the regime. Look at Bin Laden, Venezuela, and Iran as foundations.

2.  No idea on time to complete, but I think it'll start early next year at latest.

3.  New government, treaties, heavy investment, dead Castro loyalists that decide to stay in Cuba.

 

 

[VeguerosMAN]

On 6/19/2026 at 1:12 AM, Dadof3 said:

Starving the population is not going to bring about meaningful change in the government is my guess. If the US is just going to continue the blockade and various sanctions, Trump will almost certainly get bored and turn his attention to something else at some point and nothing will really change. I think the bribery method would work best.  

"Money makes you do things you don't want to do." I am pretty sure the rats within the regime already got their money when the CIA director visited the island and it's only a matter of time when they start ratting out.  

[JohnnyO]

On 6/17/2026 at 7:08 PM, chris12381 said:

For context: I've been running an ongoing US-Cuba analysis with Claude (Anthropic's AI) for a few months now. Not casual chat. I built a dedicated project tracking GAESA, the Rubio pressure campaign, the Brothers to the Rescue case and the Raul Castro indictment, the Helms-Burton litigation, and the energy crisis, and I've been feeding it primary sources and making it show its work. So when you posted these three questions, I ran them through that setup. What follows is its answer, lightly edited. I made it flag which claims rest on a single anonymous scoop versus what's actually confirmed, and I told it to discount Trump's "soon" rhetoric since that's been wrong for 30 years. Take it for what it is: a structured guess, not gospel.

"Quick pushback before I answer: I don't think this is the "final phase." Calling it that is the same trap that's burned every Cuba-watcher since 1991. The siege is real and it's biting harder than anything since the Special Period, but "effective" and "about to end" are different claims.  Here's how I'd actually answer your three.

1.  How does it end / what's the process?

Most likely it doesn't end clean, at least not soon. The realistic path is a grind: more sanctions, more back-channel talks that go nowhere, the occasional concession from Havana (they've already dumped 2,000+ prisoners) that doesn't satisfy Rubio, because Rubio's actual demand is the regime itself, which is Havana's one red line. Two sides whose bottom lines can't both be true equals stalemate, not a deal. If it does resolve, watch GAESA, not Díaz-Canel. The real talks are reportedly already running through the military conglomerate and Raúl's grandson, not the formal government. An elite cutting itself a soft landing (think USSR 1991, not a clean democratic handoff) is the most plausible off-ramp. The other live path is the ugly one: a Maduro-style snatch using the Castro indictment as the legal hook. Possible, but Cuba's a harder target than Venezuela was. No single guy to grab, a much tighter security state, and Díaz-Canel promising a bloodbath for any invader.

2.  How long?

Don't hold your breath for 2026. The Iran deal just freed up the bandwidth everyone said was the holdup, and Trump's first move was to point it at Ukraine and Lebanon, not Cuba. Revealed priorities beat tweets. Add the midterm math: Florida wants action, but a Mariel-scale boatlift right before November is the last thing the border crowd wants. I'd put a regime-ending event this calendar year at maybe one-in-four to one-in-three, and basically nil in the next month barring something I can't see. Trump's "soon" is worth nothing on timing. He claimed an Iran deal was imminent something like 38 times before one actually landed.

3.  Post-conflict Cuba

Base case, and I don't love it: the regime survives in worse shape. More militarized, more repressive, GAESA running even more of the economy, leaning harder on Russia and China to keep the lights on.  Sanctions that wreck the civilian economy tend to entrench the guys holding the hard currency and the guns, which is exactly GAESA. The rosier version is a managed opening: elite-brokered transition, partial market reforms, heavy US/Treasury leverage over the books, Vietnam-ish. The version nobody should want is Iraq 2003: break the state apparatus, get chaos, an exodus across the Straits, maybe an insurgency. The thing the siege-is-working crowd keeps missing is that deprivation alone has never cracked this regime. Yet, this crisis is different, and not in Havana's favor: the oil blockade and the scale of the exodus are new, and the leadership is weaker than Fidel's was. But the mechanism that actually ends regimes is the same one it's always been. Hardship topples governments by splitting the army and the elite, not by starving the street, and that split is the thing I haven't seen yet. What would change my read is mass protest significantly bigger than July 2021, or a visible crack in the security forces. Until I see one of those, I'm betting on grind, not collapse."

W-w-w-w-ait you are using AI based on rhetoric? 

1. Firings/blame game are the norm. You keep firing, you control the media. Unable to follow through, nothing is accomplished by midterms. More rhetoric. They took too long to attack their $$$ and were stupid enough to announce their "plan"

2. 2029

3. Dems take over, an Obama similar policy. Partial market reforms? WTF are you talking about? Business is as usual. 

[El Presidente]

Hmmm.

 

1. Iran was a disaster by any coherent measure for Trump. Whoever advised him won't be in the good books and certainly advice on Cuba strategy by the same ignoramus would (you hope) be frowned upon.

2. Read the Cuban Govt foreign investment announcement policy of four days ago. General Cigar USA with US gov approval could buy into Tabacuba/Cubatobacco/Habanos...Now.  

Interestingly, foreign companies cannot without facing US gov sanctions. 

I suspect a lot more is going on below the surface than is being announced. I pray someone is calling the plays intelligently on both sides. 

Gut feel. Done by August 1. 

[Dadof3]

16 hours ago, El Presidente said:

Hmmm.

 

1. Iran was a disaster by any coherent measure for Trump. Whoever advised him won't be in the good books and certainly advice on Cuba strategy by the same ignoramus would (you hope) be frowned upon.

2. Read the Cuban Govt foreign investment announcement policy of four days ago. General Cigar USA with US gov approval could buy into Tabacuba/Cubatobacco/Habanos...Now.  

Interestingly, foreign companies cannot without facing US gov sanctions. 

I suspect a lot more is going on below the surface than is being announced. I pray someone is calling the plays intelligently on both sides. 

Gut feel. Done by August 1. 

If American companies are going to get US government approval to do anything both the private sector and the government are going to need a full scale revision of Cuban policy. That's a big ask. It can certainly happen but given how slow the US is to act it's hard to see it going smoothly or swiftly. Trump will have the Cuban expat community in Florida upset and maybe some other companies that will be embroiled in trademark litigation and the like. We will see. I hope whatever happens is consensual and works for the regular Cuban citizens on at least some level. 

[Christophe]

On 6/18/2026 at 8:12 AM, El Presidente said:

1. How does this end. What does that process look like? 

2. How long before this ends?

3. What is the likely end position? When all said and done, describe the post conflict/negotiation Cuba. 

1. Probably some orchestrated government overthrow. Cuban intelligence can't be that good, with the limited means they have. There have to be aspiring elites within Cuba that are disgruntled and decide at some point they have more to gain from working with the US than remaining in their current position. Couple that with some color-revolution, maybe some bombs for democracy and voila...regime change. Depending on how recalcitrant the old regime elements are, years of low-intensity conflict and terrorism. 

2. A few years at most. I don't think the US will exist as a hegemony a couple decades from now, but Cuba probably can't outlast them at this point. 

3. The US is not interested in some middle ground. They want hegemony. Probably gonna look like Venezuela + some resorts. Maybe they'll get something out of American tourists. But probably not a decent living wage for the Average Juan by any means.

[VeguerosMAN]

17 hours ago, Dadof3 said:

If American companies are going to get US government approval to do anything both the private sector and the government are going to need a full scale revision of Cuban policy. That's a big ask. It can certainly happen but given how slow the US is to act it's hard to see it going smoothly or swiftly. Trump will have the Cuban expat community in Florida upset and maybe some other companies that will be embroiled in trademark litigation and the like. We will see. I hope whatever happens is consensual and works for the regular Cuban citizens on at least some level. 

I think the only way this for this to work is a complete regime change. The current Cuban regime is just buying time. At least the US is making "deals" with a new regime in Iran as 400 of their past ministers are gone. I just don't see the US sitting at the same table with the Castros and the current regime to make any sort of deals.  

[El Presidente]

7 hours ago, VeguerosMAN said:

. At least the US is making "deals" with a new regime in Iran 

[JohnnyO]

I was there this weekend and without power 2 days. No explanation as to the reasons, no excuses. They are not putting the World Cup on, even in delayed format or the airport. These extended outages are taking a toll on everyone, especially when they have to throw away food. Recently they implemented a rule that locals can't travel more than 50 kilometers from their home. You need a letter to travel inside the country. The purpose is so that they can control locals in case there is an uprising. About a block from where I stay there was a local that had a MYPIME. He sold beer, powdered, milk etc and changed dollars. He's in jail now, not sure of the charges and they took everything away. Pretty sure it was related to his 2 sets of books. Speculation is he might get 8 years. Now they are saying they want free market reforms, so shouldn't this guy get out of the can? No, they are going to throw the book at him. At the moment I can import a 10 year old SUV for the cost of $14,000+. Last Thursday they had a writeup in Granma that listed 1000's of things they are going to do. One of them was removed duties for imported vehicles. When will this be? Christmas or 2050? Added to that they have taken vehicles from locals for improper paperwork or because they had too many. No fine, hearing in court, you just lost your car forever. So they will "say" things and do "deals" but what's behind door #3 is another surprise when you get there. They have dedicated their life to lies, deception and jedi-mind-tricks and now you are going to believe them? Let's all have a beer and a good laugh. John

[VeguerosMAN]

7 hours ago, JohnnyO said:

I was there this weekend and without power 2 days. No explanation as to the reasons, no excuses. They are not putting the World Cup on, even in delayed format. These extended outages are taking a toll on everyone, especially when they have to throw away food. Recently they implemented a rule that locals can't travel more than 50 kilometers from their home. You need a letter to travel inside the country. The purpose is so that they can control locals in case there is an uprising. About a block from where I stay there was a local that had a MYPIME. He sold beer, powdered, milk etc and changed dollars. He's in jail now, not sure of the charges and they took everything away. Pretty sure it was related to his 2 sets of books. Speculation is he might get 8 years. Now they are saying they want free market reforms, so shouldn't this guy get out of the can? No, they are going to throw the book at him. At the moment I can import a 10 year old SUV for the cost of $14,000+. Last Thursday they had a writeup in Granma that listed 1000's of things they are going to do. One of them was removed duties for imported vehicles. When will this be? Christmas or 2050? Added to that they have taken vehicles from locals for improper paperwork or because they had too many. No fine, hearing in court, you just lost your car forever. So they will "say" things and do "deals" but what's behind door #3 is another surprise when you get there. They have dedicated their life to lies, deception and jedi-mind-tricks and now you are going to believe them? Let's all have a beer and a good laugh. John

Did you stay at a hotel or a casa particular in Havana? I am thinking about going back there in August from the US - the prices of casa particulars are so cheap now.  

[El Presidente]

7 hours ago, JohnnyO said:

 So they will "say" things and do "deals" but what's behind door #3 is another surprise when you get there. They have dedicated their life to lies, deception and jedi-mind-tricks and now you are going to believe them? Lets all have a beer and a good laugh. John

John, this would be the 8th or 10th "announcement" of SME business liberation over the past 25 years. None have amounted to squat. 

[JohnnyO]

6 hours ago, VeguerosMAN said:

Did you stay at a hotel or a casa particular in Havana? I am thinking about going back there in August from the US - the prices of casa particulars are so cheap now.  

Casa particular but I have my own generator. I buy my own gas at $29/gallon, used 5 gallons while I was there. I paid a local to stand by in the midnight hour to fill it up if it ran out of gas. Nothing like trying to fill a generator at 3am after 10+ beers. You might have some hurricane weather in August, if it's a bad one they definitely shut off the power. Wherever you are going, make sure they have a generator that can run AC and have backup gasoline. The mosquitos are plentiful. There are many hotels that have generators but not enough for AC. John